Abstract
2-(1-Oxido-2-pyridinio)-3-phenyl-4 (3H)-quinazolinone (1), 2-(1-oxido-2-pyridinio)-3-phenyl-4 (3H)-quinazolinone 1-oxide (4) and their control compounds, 3-phenyl-2-(2-pyridyl)-4 (3H)-quinazolinone (6) were nitrated under appropriate conditions, to give 3-(3-nitrophenyl)-2-(1-oxido-2-pyridinio)-4 (3H)-quinazolinone (2), 3-(3-nitrophenyl)-2-(1-oxido-2-pyridinio)-4 (3H)-quinazolinone 1-oxide (5) and 3-(3-nitrophenyl)-2-(2-pyridyl)-4 (3H)-quinazolinone (7) as mononitro-derivatives or 6-nitro-3-(3-nitrophenyl)-2-(1-oxido-2-pyridinio)-4 (3H)-quinazolinone (3) and 6-nitro-3-(3-nitrophenyl)-2-(2-pyridyl)-4 (3H)-quinazolinone (8) as dinitro-derivatives, selectively and in comparatively higher yield. Next, compound (6) was halogenated with bromine, NBS and NCS by varying reaction temperature and concentration of sulfuric acid, and by adding silver sulfate as an activator, to give 3-(3-bromophenyl)-2-(2-pyridyl)-4 (3H)-quinazolinone (10) and 6-bromo-3-phenyl-2-(2-pyridyl)-4 (3H)-quinazolinone (12) as monohalogenides and 3-(3, 4-dibromophenyl)-2-(2-pyridyl)-4 (3H)-quinazolinone (11), or 6-bromo-3-(3-bromophenyl)-2-(2-pyridyl)-4 (3H)-quinazolinone (13) as dihalogenides, and further to give a derivative which was presumed to be a trihalogenide.
